Beta-mercapto-propionic acid anthraquinone dye



Patented May 27, 1930 UNITED STATES PATENT OFFICE HERMANN BEBTHOLD, OFLEVERKUSEN-ON-THE-RHINE, GERMANY, ASSIGNOR T GEN- ERAL ANILINE WORKS,mo, OF NEW YORK, N. Y., ACORPORATION OF DELAWARE fl MERCAI'TO-PROPIONICACID ANTHRAQUINONE DYE No Drawing. Application filed December 16, 1927,Serial No. 240,641, and in Germany December 18, 1926.

The present invention concerns sulfur containing dyestuffs of theanthraquinone series. They can be obtained by subjecting mercaptans ofthe anthraquinone series to the action of halogen substituted higherhomologues of acetic acid. The new sulfur dyestuffs dye esters andethers of cellulose or the conversion products thereof e. g.hydrocellulose very intense golden yellow shades, which are very fast.

The new products are in the form of their alkali metal salts after beingdried and pulverized generally colored powders soluble in water." In thefree state they have most probably the following formula:

i f) Q color change.

RSR1CO OH wherein R stands for an anthraquinone radicle which may besubstituted, R stands for an alkylene radical containing at least twocarbon atoms e. g.

The following examples will illustrate my invention:

EwampZe 1.--l part by weight of anthraquinone-l-mercaptan and 20 partsby weight,

of 5% alcoholic caustic potash are heated together until a solution ofl-anthraquinonepotassium-mercaptide is obtained, which is decomposed byheating for a short time at the boiling point-with an alkaline solutionof ,B-chloro-proprionie acid, until the formation of the potassium saltof anthraquinonyl-B- mercapto-propionic acid occurs having the formula:

which is ascertained by the accompanying culent precipitate.

For dyeing, one gram of the sodium salt is made into a paste wlth 1 gramof Marseille 53 soap, using water free from CaCO and the Afterfiltration and acidifica tion, the dyestufi' separatesas a yellow,flocfi-mercaptopropionic acid is obtained from laminoanthraquinone-4-mercaptan as .described in the previous example; thedyestuffs dyes cellulose acetate silk in blueish-rose shades.

I claim:

1. The products having in their free form the probable formula:

V o sonioniooon Q0 ll wherein the anthraquinone nucleus may be furthersubstituted, said products being in form of their alkali metal saltscolored powders', soluble in water, dyeing cellulose acetate silk strongand fast shades.

2. The product having in its free form the probable formula:

0 S.CH2.CH2.COOH

g QC said product being in form of its sodium salt a yellow compound,yielding on cellulose acetated silk a strong and fast; golden yellow s ae.

3. Cellulose acetate silk dyed with a dyestuif of claim 1.

4. Cellulose acetate silk dyed with the dyestuff of claim 2.

In testimony whereof I have hereunto set my hand.

. HERMANN BERTHOLDL lUU

